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A Salesman’s Guide to Everyday Conversation With Strangers

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One of the most valuable traits a salesperson can possess is the ability to easily strike up conversations with anyone who crosses their path. Whether you’re on a plane or in line at the grocery store, having a method for starting a conversation with random strangers is an asset that sets the best apart from the mediocre. This ability correlates into more sales as every new person you talk to becomes a new prospect for you to pitch your services to.

Since sales is something that all of us do every single day (you do not have to always be bartering or selling something for money to be selling something), the five steps below have proven to help out a lot of people with their sales career and confidence to network when around people they don’t know.

Here are my 5 proven steps to starting a conversation with anyone:

1. Paralleling

This step is super effective and easy. The trick is identifying what the other person cares about. Things like tattoos and jewelry are great examples of personal attributes or items that they cherish and or that mean something to them. 

Ideally, you want to identify something they have that you have yourself. This becomes an easy way to strike up a conversation and build rapport by being “like” them. For example, on a recent trip, I noticed that the guy sitting next to me had Chinese characters in the tattoo on his arm. From here, we can move into…

2. 20 Questions

Here we start asking them questions about the item or attribute that we identified in the paralleling step. Be sure to make eye contact, smile and approach the questions with a relaxed, yet interested energy. If they feel like you are forcing the conversation, it will make them uncomfortable and clam up.

Remember the tattooed guy on the plane? After I asked him what the Chinese characters meant, the door was open to ask further questions, like “That’s really cool, what made you get the tattoo?”

To make it easy, create questions fusing who, what, when, where and how, which allows the person you’re talking to to tell a story about themselves. This creates a bond and builds trust with them quickly because they feel admired and liked. You’d also be amazed at how much you can find out about someone by doing this.

However there is a warning here! There is a way to screw this up! The item or attribute you are paralleling needs to be something you genuinely like and are interested in. This is key. So if you know nothing about tattoos, don’t want a tattoo, or don’t like tattoos, then don’t compliment them on their tattoo, because it will be disingenuous and you won’t be contribute back to the conversation. In other words, you will lose the bond with the person you are communicating with really quickly.

“To be interesting, be interested.” – Dale Carnegie 

3. You’re My Hero

If you have asked enough questions you should have a general idea from the person you are talking to and you now can use that information to connect with them on other levels of common interest.

Find life circumstances that match or stories that you share. Tell them how something in their story moved you emotionally (make sure to be genuine!) or help the person emotionally see and feel how their story connected with you. This will help to initiate the first “bonding moment” that you two share.

We call this step of this process, “you’re my hero” because you have shown excitement around something they do that you wish to do or do yourself. This “likeness” helps strengthen the bond and open up the other person to share more about their life with you.

4. Common Denominators

By now you’ve asked some questions, gotten some information from them, and heightened the bond between the two of you. You can keep the conversation going by mentioning other things that you like and notice that you two might have in common, based either on physical things you see or answers to your questions. 

Each “common denominator” you can find serves to tighten the bond between you and them. The stronger the bond you can develop with them, the more powerful the last step will be!

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” – Dale Carnegie

5. Leave Behind

Here is where you make this conversation stick in their memory. All four others steps lead to this, because it’s where you can leverage the conversation and connection into some sort of transaction. 

This transaction doesn’t always mean a sale, it can occur in a range of ways. You may have a person to introduce them to that can solve their challenge, or you may be able to send them a referral, or it could be as simple as a business card exchange or friending them on social media.

A popular leave behind in 2019 is a mobile app, mainly because someone always has their phone with them. A leave behind is a way for them to have your contact information (and you get theirs) so you can connect with them after the conversation is over. Other great leave behinds are a copy of a book you wrote, your website link, or a sales funnel link.

Sometimes too, when things go really well with the conversation (believe me, you will know) you may be able to immediately schedule a time to talk with them later. The bond needs to be strong enough before you propose this because if it’s not it can ruin this entire opportunity.

If you’re thinking this sounds simple, you’re right! And it still takes practice to perfect. For some seasoned sales people, they can probably think back to a time or two when they did this unconsciously and it worked out great. The thing is, when you practice these steps and allow it to become an unconscious process you can use too, it can be a lethal weapon for you in your professional career and your life as a whole.

Start by practicing the steps consistently. Practice at the gym, at restaurants, anywhere you are where there is a stranger nearby. Over a short period of time you’ll accrue a lot more contacts, have the opportunity to make more sales and you’ll become such a natural that people will think you were born charismatic! 

What part of this salesman’s guide resonated most with you and why? Share your thoughts with us below!

Sidney Clevinger is a social media influencer, coach, and presenter that specializes in helping entrepreneurs and business owners leverage their social media so they grow their business following a specific and emotionless 3 Pillar Formula that includes lead generation, conversion and retention. Sidney works with clients and runs courses all over the world. He believes that everyone was put on this earth with a gift to share, and leveraging your social media to increase your influence is a great place to do that. Sidney has a range of valuable resources for people to understand how to leverage their social media and attract customers for their products on his YouTube channel, Facebook Page, or FREE Social Media Program, "Better Leads 7-Day Social Media Bootcamp."

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Success Advice

How to Achieve Massive Success Without Crushing Your Soul

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Image Credit: Addicted2success

Most highly ambitious people suffer from a dangerous illusion: the belief that if they can just achieve one more milestone—a funding round, a promotion, an exit—they will finally feel like they are enough.

Entrepreneurs and leaders will sacrifice their sleep, relationships, and sanity to reach that distant horizon. But when the big payday or the massive accolade finally arrives, a terrifying reality sets in: nothing changes. The external world shifted, but the internal emptiness remained. Trying to find internal validation through external achievement is like drinking saltwater to quench your thirst; it seems like it will work, but it only leaves you thirstier.

High achievers are always playing two games in parallel:

  1. The External Game: Your career, your income, your accolades, and your status.
  2. The Internal Game: Your relationship with yourself, your peace, and your self-worth.

You can have white-hot ambition, make incredible money, and build a meaningful legacy without burning out. But to win without crushing your soul, you must master metacognition—the ability to reflect on and control your own thinking.

Here are three profound internal shifts you must make to beat high achiever burnout and build a life you actually enjoy.

1. Fire Your Internal Coach

Most ambitious people are driven by a ruthless inner monologue. This internal “coach” constantly whispers that your value is strictly tied to your performance. If you fail, you are worthless.

Many high achievers justify this abusive inner voice. They believe it gives them their edge and keeps them motivated. But if you step back and truly observe that voice, you will notice something profound: your inner critic rarely offers actionable solutions or brilliant ideas. It only offers fear.

That toxic internal coach is simply your own fear incarnated—fear of failure, fear of rejection, and fear of not being enough. Worse, this doesn’t just hurt you. When you operate from a place of self-loathing and fear, you project that negativity onto your team, your business partners, and your family.

You cannot cultivate healthy relationships with others if your relationship with yourself is toxic. To reach the next level of leadership, you must fire that coach. Give yourself permission to stop beating yourself up, and consciously shift from being your own harshest critic to being your strongest ally.

2. Pull the Nails Out of Your Head

Imagine a person complaining about a blinding, chronic headache while completely ignoring the obvious iron nail sticking out of their forehead.

In business and in life, we all accumulate metaphorical nails. Your nail is the obvious problem you are actively avoiding. It might be a co-founder relationship that has turned toxic. It might be a failing product line you are too stubborn to cut. It might be a destructive personal habit, or a deep-seated trauma you have refused to address.

We leave these nails in our heads for one simple reason: pulling them out hurts.

To reach the next peak of success, you have to realize that growth is not a straight upward line. To get off a stagnant plateau, you must first traverse a valley. If you fire a toxic client, you will face temporary financial stress. If you quit a bad habit, you will face temporary discomfort.

Something has to get worse before it gets better. But everything you truly want is on the other side of that temporary valley. Facing your fears and pulling out the nails is a superpower. Endure the short-term pain, and watch how fast you elevate once you are finally free of the friction.

3. Trust Your Second Voice

The voice of fear and criticism is not the only voice in your head. You have a second voice—your intuition.

Unlike your inner critic, your intuition does not speak through panic or fear; it speaks through energy. Energy is the language of your true ambition.

When you think about a project you feel obligated to do out of societal pressure, your energy lags. You feel a heavy sense of dread. But when you think about an idea you are secretly terrified of but deeply passionate about, your energy spikes. You feel electricity.

In almost every major business or life decision, you already know the answer. Your intuition has already told you what to do; your hesitation is simply a negotiation with your fear.

How do you conquer that fear? Write it down. Fears are incredibly dangerous when they lurk as nebulous clouds in your subconscious. When you put them on paper, they lose their paralyzing power. They cease to be monsters and simply become standard problems to be solved. And as an entrepreneur, you are an expert at solving problems.

Stop Waiting for the Destination

It is easy to look at the grind of building a business and think, “I’ll be happy when I finally sell this company,” or “I’ll relax when we hit $10 million in ARR.”

But the point of the journey is not the destination. The point of the flight is not simply to land; it is to experience the magic of being in the air.

Stop postponing your happiness for a future that is not guaranteed. Fire your toxic internal coach, do the hard work of pulling out your nails, and follow the energy of your intuition. You have already arrived. You are living in the “good old days” right now—make sure you are actually present enough to enjoy them.

Here is a great speech by Graham Weaver about How to Win Without Crushing Your Soul

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Success Advice

Why Your Morning Routine Needs a Document System, Not Just a To-Do List

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Image Credit: Addicted2success

Most morning routines are built around a mindset. A journal entry, a cold shower, ten minutes of stretching, or a fixed order for coffee and email, each one designed to start the day with focus. What almost never makes that list is the paperwork already sitting in your inbox from yesterday: the contract still needing a signature, the invoice a client asked you to resend, the intake form HR needs before nine o’clock.

A checklist can remind you these tasks exist, but it cannot tell you where the file lives, what format it needs to be in, or how many versions sit on your desktop already. That gap is why a document system matters more than one more app for tracking tasks.

The Piece Most Routines Skip

A to-do list can capture a single line such as send the signed lease, but the real work behind that line is gathering three or four separate files into one place first. A simple habit handles this well: before opening email, pull yesterday’s scans, forwarded attachments, and signed pages together into one working file. Open a PDF combiner to merge those pieces into a single document, and the visible task, actually sending the file, only takes as long as it should.

This is not just about signatures or contracts. Recurring items such as monthly reports, vendor invoices, and reference documents pile up the same way, and a five-minute pass each morning keeps them from becoming a bigger cleanup later in the week.

This is not a small pocket of wasted time either. The most recent Bureau of Labor Statistics time use data groups tasks like filling out paperwork together with other household management activities such as cooking and yard work, and finds that adults spend close to two hours a day on that broader category. A five-minute document habit each morning is a modest trade against that total, and it moves the drag to the start of the day instead of letting it bleed into everything after.

A Three-Layer System That Fits in Fifteen Minutes

A working system for morning paperwork does not need folders inside folders. Three layers cover almost everything:

  • Needs action today: Anything someone is waiting on, like a contract to sign or a form due before noon, gets handled first.
  • Reference only: Files you might need to check but do not have to touch, such as a signed agreement from last month, stay in a folder you can search instead of one you have to scroll through.
  • Archive: Anything finished and no longer active moves out of daily view completely, so it stops competing for attention with today’s work.

These three buckets take less time to sort into than most people spend deciding what to have for breakfast.

Three Small Habits That Make It Stick

None of this needs new software training or a rebuilt inbox. A few small habits carry most of the weight.

  • Keep one working file: Combine incoming pages into a single document each morning instead of juggling several attachments across separate emails.
  • Check who needs access, not just who has the file: Confirm the person waiting on a document (a client, a coworker, a new hire) can open it under their own account, since being able to share a PDF on any device matters more than which laptop or phone you used to finish it.
  • Close the loop by noon: Move anything finished into reference or archive so tomorrow’s list starts smaller instead of longer.

Each habit takes under a minute on its own, and together they keep paperwork from stacking up into a Friday-afternoon problem.

Different Roles, Same Morning Problem

The specifics change by job, but the underlying gap stays the same across roles.

Freelancers often start the day with three or four client threads open at once, each with its own estimate, contract, or invoice version, and a quick merge each morning keeps those from scattering across a downloads folder.

HR staff run into a version of the same problem multiplied across every new hire moving through onboarding at the same time, since offer letters, tax forms, and identification copies all need to land in one file before anything gets filed.

Designers hit it from another angle: client feedback often arrives as a photo of a printed mockup or a screenshot of a marked-up page, and turning those images into one proper document is the real first step before revisions can begin.

None of this calls for a full overhaul of how you work. It just means treating documents as part of the routine instead of an afterthought that shows up once the coffee is gone. Fifteen minutes spent sorting real files into a real structure each morning saves more time by lunch than another motivational routine ever will, and it is the difference between reacting to paperwork all day and starting ahead of it for once.

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The Psychology of Power: How to Win the Mind Games of Business

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You might think that your business is driven by data, analytics, and perfectly optimized algorithms. But beneath the spreadsheets and KPIs, the business world is driven by something far more primitive: human psychology.

Robert Greene, the mastermind behind The 48 Laws of Power, has spent decades studying how top executives, historical figures, and entrepreneurs navigate strategy. His conclusion? Human behavior is compulsive, obsessive, and entirely predictable if you know what to look for.

Whether you are scaling a startup, navigating corporate politics, or trying to understand why a competitor is outmaneuvering you, success rarely comes down to who works the hardest. It comes down to who understands the social game. Here is a breakdown of Greene’s most potent strategies for mastering the psychology of business.

1. The Art of Concealing Intentions

Is honesty really the best policy in business? According to Greene, the answer is a resounding no—at least, not with everyone.

When dealing with your internal team, transparency is essential. A leader must have a clear vision and communicate it directly so the organization can execute without chaos. However, when it comes to your competitors, complete transparency is a fatal flaw.

If your rivals know exactly where you are headed, what your next product launch looks like, or what your strategy will be in six months, they will mirror you and counter your moves. The game of power is subtle. To win, you must keep your competitors—and sometimes even your clients—on their heels. By concealing your true intentions, you force your rivals into a defensive posture, leaving you in control of the offensive.

2. Why Silence is Your Greatest Leverage

In the corporate world, there is a misconception that the loudest person in the room is the most powerful. Greene argues the exact opposite: talking less creates an aura of power.

When writing The 50th Law with 50 Cent, Greene observed the rapper in high-stakes business meetings. 50 Cent would sit in absolute silence while others talked, causing everyone else in the room to over-explain, backtrack, and ultimately reveal their insecurities.

  • The psychology behind it: When you talk constantly, you signal insecurity and a lack of self-control.

  • The power of silence: When you remain quiet, people project their own anxieties onto you. They wonder what you are thinking. It makes you appear larger, more mysterious, and more authoritative than you actually are.

Every word you say should be strategic. If you cannot control your own mouth, you cannot control your environment.

3. Formlessness: Adapt or Die

Many leaders rise to the top based on a specific strength—maybe it is ruthless aggression, brilliant public speaking, or a populist touch. But holding onto the trait that made you successful is the fastest way to become obsolete.

Borrowing from Machiavelli and Sun Tzu, Greene emphasizes the law of formlessness. The business landscape is shifting constantly; what worked three years ago is likely irrelevant today. If you are rigid in your brand, your personality, or your strategy, the world will pass you by.

Consider a brand like American Apparel, which thrived in the early 2000s on a very specific, nostalgic, 1980s aesthetic. When consumer tastes shifted in 2009, leadership refused to adapt. They clung to the form that brought them initial success, and it ultimately led to their downfall. True power belongs to the leader who can reinvent themselves and change shape to fit the times.

4. Never Outshine the Master (Navigating Ego)

This is arguably the most critical workplace law to engrave into your brain: everyone has an ego, and everyone has insecurities.

If you are an employee working under a boss, your natural instinct is to work incredibly hard, do a brilliant job, and take all the credit to prove your worth. But if you try too eagerly to impress and you end up soaking up all the attention, you will trigger your boss’s insecurities. Unconsciously, they will start viewing you as a threat.

To survive and advance, you must master the nuanced art of letting the person above you take some of the glory.

  • Do the heavy lifting.

  • Present the wins.

  • Let your superior feel as though it was their visionary leadership that made it possible.

It might feel unfair, but reacting emotionally to this dynamic drains your energy. Accept that taking a strategic backseat is simply part of the power game. By stroking the ego of the person above you, you secure your position and quietly build your own leverage.

5. Despise the Free Lunch (and Appeal to Self-Interest)

In business, free is the most expensive mistake you can make. When someone offers you something for free, they almost always want something far more valuable in return. On the flip side, being cheap with your money—refusing to pay your employees well or constantly seeking a bargain—signals weakness and a lack of abundance.

When you need something from a powerful person, do not appeal to their mercy. Do not remind them of a past favor or ask for help out of the goodness of their heart. Instead, appeal strictly to their self-interest.

Powerful people lack two things: time and attention. If your proposal can save them time, organize their chaos, or solve a specific insecurity they have, they will be eating out of the palm of your hand.

The Ultimate Shift: Outward Focus

The single most important skill you can master in business is shifting your focus outward. Stop obsessing over your own needs, your own emotions, and whether people like you. Instead, become a master observer of the social game. Watch the trends, study your competitors, and fiercely analyze the unspoken needs of your clients. When you stop acting out of emotion and start acting out of strategy, the entire game changes.

Here is a powerful breakdown with Mark Brazil and Robert Greene

 

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Success Advice

Why Hustle Culture is Burning Founders Out (And What to Do Instead)

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Image Credit: Addicted2success

An entire generation of founders has been conditioned to idolize the “grind.” The dominant philosophy in today’s founder culture centers heavily on sacrifice, pushing to your limits, out-working everyone else, and sheer, ruthless execution.

While building something great absolutely requires push and sacrifice, relying solely on the hustle method often leads to severe long-term consequences. Founders who only know how to grind frequently find themselves financially successful but spiritually and mentally bankrupt. They end up losing the most important things in their lives because they were entirely consumed by a singular goal.

Ultimately, many entrepreneurs accidentally build a prison and call it a business. They find themselves stuck on a hamster wheel, constantly chasing the next milestone without ever feeling like they have achieved enough.

If you have already figured out the basics of business but feel a deep lack of joy—if you are holding on too tight, lacking presence, and feeling like something is “off”—it is time to rethink your operating system. Shifting from a mindset of force to a mindset of alignment can counterintuitively make you happier and more present, while simultaneously causing your business to grow even faster.

The Shift: From Ruthless Execution to Work as Play

What is the fundamental difference between the traditional hustle mindset and the alignment mindset?

  • Execution vs. Play: Hustle culture advocates for ruthless execution, advising founders to just do the work whether they feel like it or not. The alignment philosophy argues that you must find work that feels like play to you, but looks like work to others. Sheer force and ambition are not enough to make a meaningful contribution; you must actually enjoy the act of what you are doing.

  • Time Horizons: The grind mindset focuses heavily on short-term actions, placing extreme importance on what you can force to happen today. Alignment looks at a much longer time horizon, focusing on your life’s work and your unique, long-term contribution to the world.

  • Escaping Competition: Hustle culture teaches that you beat the competition through a massive volume of work. Alignment argues that you escape competition by finding a path so uniquely yours that nobody else can possibly compete with you. You stop playing a game where someone else made the rules, and you start leaning entirely into your authentic self.

The Danger of Force and Fear

Applying constant force to your business ultimately creates a counterforce. When you force things constantly, it often manifests negatively in your daily life. You may find yourself getting easily annoyed in traffic, dealing poorly with strangers, or resenting your partner.

Habits and emotions compound over time. If you compound negative emotions and counterforce daily—constantly swimming against the current instead of finding it and riding it—it leads to a miserable existence. Conversely, compounding joy and inspiration leads to unimaginably great outcomes.

Furthermore, the constant push to outwork others usually stems from fear. Whether it is the fear of losing a client, feeling unworthy, or worrying about not being accepted, pushing out of fear often causes founders to subconsciously attract the exact negative outcomes they are trying to avoid.

Understanding Life Cycles and Alignment

Alignment with your work is not permanent; humans live in cycles that typically last between four to eight years. During each cycle, a core theme—such as a specific work project, a family focus, or a personal struggle—rules your life.

What feels incredibly aligned today might fall completely out of alignment tomorrow as you reach the end of a specific cycle. It takes incredible presence, awareness, and humility to walk away from something you spent eight years building once it is time to discover your next step. But that evolution is a mandatory part of a fulfilling life.

When You Actually Need the Hustle

This isn’t to say that grinding is useless. The advice to take relentless action regardless of how you feel is excellent entry-level advice for young entrepreneurs. In the beginning of your career, you need to put in the reps, gather data, and gain experience just to discover what you actually like, what you are good at, and what the market responds to.

However, once a founder has gathered enough feedback, figured out the basics of business, and gained self-awareness, the raw hustle philosophy becomes a liability. At that stage, you must prioritize fulfillment and lean into what feels aligned. You have the data; now it is time to build something that doesn’t just make money, but actually makes you feel alive.

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